Succinonitrile

Succinonitrile, also butanedinitrile, is a nitrile, with the formula of C2H4(CN)2. It is a colorless waxy solid which melts at 58 °C.

Succinonitrile
Skeletal formula of succinonitrile
Ball and stick model of succinonitrile
Ball and stick model of succinonitrile
Spacefill model of succinonitrile
Spacefill model of succinonitrile
Names
Preferred IUPAC name
Butanedinitrile[1]
Other names
  • Deprelin
  • Dicyanoethane
  • Ethylene cyanide
Identifiers
3D model (JSmol)
1098380
ChemSpider
ECHA InfoCard 100.003.441
EC Number
  • 203-783-9
MeSH succinonitrile
RTECS number
  • WN3850000
UNII
  • InChI=1S/C4H4N2/c5-3-1-2-4-6/h1-2H2 checkY
    Key: IAHFWCOBPZCAEA-UHFFFAOYSA-N checkY
  • N#CCCC#N
Properties
C4H4N2
Molar mass 80.090 g·mol−1
Appearance Colorless, waxy crystals
Odor odorless[2]
Density 985 mg mL−1
Melting point 58 °C (136 °F; 331 K)[3]
Boiling point 266.1 °C; 510.9 °F; 539.2 K
130 g L−1
Vapor pressure 300 Pa (at 100 °C)
Thermochemistry
145.60 J K−1 mol−1
191.59 J K−1 mol−1
139.3–140.4 kJ mol−1
−2.2848–−2.2860 MJ mol−1
Hazards
GHS labelling:
GHS07: Exclamation mark
Warning
H302, H315, H319, H335
P261, P305+P351+P338
Flash point 113 °C (235 °F; 386 K)
Lethal dose or concentration (LD, LC):
450 mg kg−1 (oral, rat)
NIOSH (US health exposure limits):
PEL (Permissible)
 none[2]
REL (Recommended)
 TWA 6 ppm (20 mg/m3)[2]
IDLH (Immediate danger)
 N.D.[2]
Related compounds
Related alkanenitriles
Related compounds
 DBNPA
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Succinonitrile is produced by the addition of hydrogen cyanide to acrylonitrile (hydrocyanation):[4]

CH2=CHCN + HCN → NCCH2CH2CN

Hydrogenation of succinonitrile yields putrescine (1,4-diaminobutane).

See also

References
  1. International Union of Pure and Applied Chemistry (2014). Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013. The Royal Society of Chemistry. p. 902. doi:10.1039/9781849733069. ISBN 978-0-85404-182-4.
  2. NIOSH Pocket Guide to Chemical Hazards. "#0573". National Institute for Occupational Safety and Health (NIOSH).
  3. Rubinstein, E. R.; Tirmizi, S. H.; Glicksman, M. E. (1990-11-01). "Long-term purity assessment in succinonitrile". Journal of Crystal Growth. 106 (1): 89–96. Bibcode:1990JCrGr.106...89R. doi:10.1016/0022-0248(90)90290-2. ISSN 0022-0248.
  4. "Nitriles". Ullmann's Encyclopedia of Industrial Chemistry (7th ed.). Retrieved 2007-09-10.


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